This invention relates to dispersions of dyestuffs and pigments in organic liquids.
There is a need in the area of solvent dispersion of organic pigments for products of lower viscosity (i.e. fluidity) and improved transparency and gloss. This is especially a need in the area of solvent inks for packaging applications. The solvents in these inks are typically oxygenated types and alcohols (ethanol, propanols), esters (ethyl acetate, isopropyl acetate) and ethers (mono methyl ether of propylene glycol), or mixtures of same. The typical resins dissolved in these solvents for formulating packaging inks are nitrocellulose, polyamide, polyurethane and polyvinyl butyrate.
U.S. Pat. Nos. 4,057,436 and 4,518,435 disclose pigment dispersions of greatly increased fluidity produced by the use of certain salts formed by the reaction of amines or quaternary ammonium salts and colored acids. However, these salts are not alkoxylated and are limited to tertiary and quaternary amine type salts.
The new compositions offer ink bases with excellent flow with improved gloss and transparency.
The present invention relates to etheramine pigment dispersing salts of the formula (I): 
wherein A is the residue of an organic pigment, x and y are each integers from 0 to 100 with x+yxe2x89xa73; and n is a number between 1 and 4.
The present invention also relates to an enhanced performance pigment composition containing a 100 parts of an organic pigment and about 1 to 40 parts of etheramine pigment dispersing salts of formula (I).
Other objects and advantages of the present invention will become apparent from the following description and appended claims.
It has surprisingly been found that the addition of an etheramine dispersing salt of the formula (I): 
wherein A is the residue of an organic pigment, x and y are each integers from 0 to 100 and x+yxe2x89xa73; and n is a number between 1 and 4, to an organic pigment enhances the dispersion of the organic pigment and greatly increases its fluidity. The etheramine salt of the invention can be added to either to a dry or a fluidized pigment. The organic pigment residue and the organic pigment can be of a different origin but preferably are of an identical origin. The organic pigment whose increased dispersion is desired is preferably substantially insoluble in organic liquid. Preferably, the origin of the organic pigment residue and organic pigment are independently selected from the group consisting of phthalocyanine, perylene, quinacridone, and carbazole violet. Both the organic pigment residue and the organic pigments may be mixtures respectively. Most preferably, the residue of an organic pigment and organic pigment are of phthalocyanine origin.
The etheramine dispersing salt of the invention is formed by reacting a sulfonic acid in an organic pigment with an ether amine of the following formula (II): 
wherein x and y are each integers from 0 to 100 where x+yxe2x89xa73; followed by isolating the etheramine salt by filtration. The synthesis of the etheramine salt of the present invention can also take place in the presence of the organic pigment whose increased dispersion is desired.
The present invention also provides for a pigment composition comprising 1 to 40 parts of the etheramine dispersing salt of formula (I) and about 100 parts of an organic pigment. The pigment composition may further comprise about 1 to 15 parts of a quaternary ammonium salt of a sulfonic acid containing pigment derivative, wherein there are from 12-60 carbon atoms in the 4 chains attached to the nitrogen atom of the quaternary ammonium ion. Preferably, the quaternary ammonium salt of the pigment is formed from a pyridinium base of the general formula (III): 
wherein R1 and R2 are each independently selected from C1-22 alkyl or alkyenyl groups. Alternatively, the quaternary ammonium salt of the fist pigment is formed from a quaternary ammonium ion of the general formula:
N+R1R2R3R4
where R1, R2, R3 and R4 are independently selected from C1-22 alkyl or alkenyl groups.
The composition of the present invention can be obtained by any of the conventional and well known methods of preparing dispersions. A preferred process for making the product of this invention comprises treating an aqueous slurry of a beta crystal copper phthalocyanine pigment with copper phthalocyanine sulfonic acid at a pH between 2-8 followed by the addition of etheramine or a mixture of etheramine and quaternary ammonium chloride. The product is then removed by filtration and dried.
As a variation of this synthesis, the copper phthalocyanine sulfonic acid may be slurried in water at a pH of 1 to 10 and the etheramine or etheramine and quaternary ammonium chloride added to this slurry.
The copper phthalocyanine pigment may be produced by any of the known arts, such as grinding with salt and glycol or dry grinding, with or without salt, and solvent treating to produce the beta crystal form.
The dispersions containing this etheramine salt may be prepared in the ink system by either adding the previously prepared composition of pigment and pigment salt derivative or by adding the individual components of pigment and derivative in the appropriate ratio.